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CS-W001157 4
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2-tert-Butyl-1H-indole

  • CAS No. 1805-65-8

  • Cat. No. CS-0060883
  • Molecule weight173.25
  • Purity≥98%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

2-tert-Butyl-1H-indole|CS-0060883

Structure of 1805-65-8

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General Information

  • CAS No. 1805-65-8
  • Cat. No. CS-0060883
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₅N
  • Molecular Weight 173.25
  • Synonym(s) 2-tert-Butyl-1H-indol
  • SMILES CC(C)(C)C1=CC2=CC=CC=C2N1

Description

2-tert-Butyl-1H-indole features a sterically hindered tert-butyl group at the 2-position of the indole core, enhancing its stability and solubility in organic media. This substitution pattern imparts favorable handling characteristics while maintaining reactivity at the nitrogen and C3 positions for downstream functionalization.

Application

2-tert-Butyl-1H-indole serves as a robust building block for indole-based scaffolds, offering enhanced stability and solubility due to the steric protection of the tert-butyl group. It facilitates electrophilic substitution at C3 and functions effectively in Pd-catalyzed cross-coupling reactions, enabling efficient access to substituted indoles. The molecule exhibits excellent bench stability and ease of purification, making it well-suited for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Smith, Keith; El-Hiti, Gamal A.; Pritchard, Gareth J.; Hamilton, Anna Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 16 p. 2299 - 2303
  • Route2
    • null|null
      116491-51-1
    • ~92%
    • In-stock
      2-tert-Butyl-1H-indole|CS-0060883
      1805-65-8

    References

    • Iritani, Koji; Matsubara, Seijiro; Utimoto, Kiitiro Tetrahedron Letters, 1988 , vol. 29, # 15 p. 1799 - 1802
  • Route3
    • null|null
      917-92-0
    • N-(2-Iodophenyl)methanesulfonamide|CS-0260516
      116547-92-3
    • ~84%
    • In-stock
      2-tert-Butyl-1H-indole|CS-0060883
      1805-65-8

    References

    • Wang, Ruiping; Mo, Song; Lu, Yongzhong; Shen, Zengming Advanced Synthesis and Catalysis, 2011 , vol. 353, # 5 p. 713 - 718

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   15.79
  • LogP   3.4654
  • H_Acceptors   0
  • H_Donors   1
  • Rotatable_Bonds   0

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